This reaction relates to the chemical synthesis of alpha-amino acids. More specifically, it relates to the reaction of the condensation product of an amine or amide and a ketone or aldehyde with carbon monoxide ("CO") in the presence of a Lewis acid solvent. The intermediate formed by that reaction is hydrolyzed, under either acidic or basic conditions, to yield an amino acid.
Amino acids, the building blocks of proteins, find wide use in nutritional therapy. Numerous chemical and biological avenues for the synthesis of alpha-amino acids have been explored in efforts to find an efficient and inexpensive means to produce these compounds. For example, U.S. No. 3,190,914 (Williams) and U.S. No. 4,073,804 (Hearon et al.) disclose chemical methods for the preparation of glycine.
Carbon monoxide chemistry has been used in the synthesis of such compounds as hydroxyacetic acid (glycolic acid). For example, U.S. No. 4,016,208 (Suzuki) discloses the preparation of hydroxyacetic acid and oxydiacetic acid by contacting carbon monoxide with formaldehyde and a catalyst consisting essentially of hydrogen fluoride. U.S. No. 3,754,028 (Lapporte et al.) discloses the production of glycolic acid, formic acid and acetic acid by the reaction of formaldehyde, carbon monoxide and water, in the presence of catalytic amounts of a Group VIII noble transition metal compound and an iodide promoter.
Amino acids conventionally are synthesized by the Strecker synthesis, Kaneko et al., Synthetic Production and Utilization of Amino Acids, p. 114 (1974). For example, glycine is synthesized by the reaction of hydrogen cyanide, formaldehyde and ammonia to form aminoacetonitrile which then is hydrolyzed to glycine.